While Gray believes he can win, the 75-year-old former mayor must weigh another consideration: Is he prepared to endure another round of attacks from The Washington Post, which went to great lengths to defeat him four years ago.

When Facebook’s data practices began dominating the news last month, The Washington Post was eager to share the story… One of the companies that profits most from closely tracking users is Jeff Bezos’ Amazon, and since 2013, Bezos has owned The Washington Post.

A review of WashingtonPost articles on Uber from this year—during which damning revelations about the company came in waves—shows that the paper is informing readers infrequently, and not at all in the past four months, that Post owner Jeff Bezos was, and presumably still is, an Uber investor.